Immersion oil

ABSTRACT

The invention is directed to an immersion oil for microscopy. The immersion oil includes an ester or ether with tricyclodecane structure as a main constituent and one or more high-boiling liquids as minor constituents. The immersion oil is free of halogens and exhibits a high UV-transmissibility and is characterized by low intrinsic fluorescence because the components utilized can be vacuum distilled.

BACKGROUND OF THE INVENTION

A substantial portion of the immersion oils offered today which have a refractive index of greater than 1.5 include chlorinated paraffin as a main constituent. Chlorinated paraffins are, however, considered to be a dangerous working substance and furthermore exhibit a poor environmental compatibility.

Halogen-free immersion oils are available in addition to immersion oils on the basis of chlorinated paraffin. The main problem in the manufacture of halogen-free immersion oils is the unfavorable relationship of the refractive index and dispersion for most of the halogen-free liquids having refractive indices having a value of greater than 1.5. The Abbe number, which describes the dispersion, deviates in such immersion oils often significantly from the range specified for DIN 58884 for the Abbe number of 44±5 (DIN) and the range ISO 8036/1 for the Abbe number 44±3 (ISO). Known halogen-free immersion oils, which have an Abbe number greater than 41, are either unsatisfactory with respect to their UV-transmissibility or exhibit an intrinsic fluorescence which is too great. Halogen-free immersion oils having values for the Abbe number in the upper tolerance range of the above-mentioned two standards (that is, with an Abbe number v_(e) >45) are not known.

European patent publication 0,209,621 discloses, in addition to halogen-containing immersion oils, also embodiments for halogen-free immersion oils. Two embodiments for halogen-free immersion oils contain tricyclodecanol as a minor constituent. With respect to the UV-transmissibility (for wavelengths below 400 nm) no information is provided by this patent publication. Furthermore, the viscosity has values of 1,000 and 2000 mm² /s at 25° C. is too great for most applications, that is, the use thereof can very easily cause air bubbles to become included.

SUMMARY OF THE INVENTION

It is an object of the invention to provide a base substance for the production of immersion oils for microscopy with which immersion oils having Abbe numbers between 40 and 50 can be produced while also having low intrinsic fluorescence and high UVA-transmissibility and being free of halogen.

The immersion oil of the invention is for microscopy and includes: as a main constituent, the tricyclodecane derivative or derivatives of substances having the basic structure of the tricyclodecane.

The immersion oil of the invention includes, as main constituents, tricyclodecane derivatives or derivatives of substances having base structures of the tricyclodecanes. The portion of the tricyclodecane derivative and/or the derivative of substances having base structures of tricyclodecanes has at least 50% by weight of the total immersion oil in the embodiments wherein the immersion oil is a two-substance mixture and at least 40% by weight for those embodiments wherein the immersion oil is a three-substance or multi-substance mixture. The immersion oil can also contain several tricyclodecane derivatives. In such cases, the sum of all tricyclodecane derivatives have at least 40% by weight of the immersion oil.

The invention proceeds from the recognition that tricyclodecane derivatives or derivatives of substance having the base structure of the tricyclodecanes exhibit a relatively high refractive index while at the same time having a high Abbe number and are therefore superbly suitable as a main component for the immersion oil. The relatively high refractive index while at the same time providing a high Abbe number is because of the ring structure of the tricyclodecanes (TCD). An immersion oil containing a TCD-derivative or derivative of substances having TCD base structure as a main constituent can therefore be free of halogen.

The derivatives of tricyclodecane as well as the substances with tricyclodecane base structures are preferably ester compounds or ether compounds. Here, esters and ethers of tricyclodecane as well as of tricyclodecane-oligomers and tricyclodecane-polymers can be considered. Also, one or several hydrogens of tricyclodecane skeletons can be substituted by other organic residues in addition to the esters and ethers of monomers, oligomers and polymers of tricyclodecanes.

In the preferred embodiments, the main constituents of the immersion oils comprise tricyclodecanemethylolester or tricyclodecanemethylolether as these liquids can be vacuum distilled because of their molecular structure and therefore provide a high degree of purity. Immersion oils having minimum intrinsic fluorescence can be produced from tricyclodecanemethylol esters and tricyclodecanemethylol ethers. The production of immersion oils to the standard values for the refractive index takes place simply by mixing the TCD methylolesters or the TCD methylolethers with suitable high boiling liquids such as softeners, paraffin oils, polypropylene glycols, et cetera.

For the production of TCD-esters and TCD-ethers, the readily available TCD-alcohols, namely, TCD-alcohol M (=8(9)-hydroxymethyltricyclo 5.2.1.0²,6 !decane) and TCD alcohol DM (=3(4), 8(9)-dihydroxymethyltricyclo 5.2.1.0²,6 !decane) which are available from Hoechst AG, Frankfurt, Germany. The tricyclodecanemethylolesters or di-(tricyclodecanemethylol)esters can be synthesized via esterification of these alcohols with dicarboxylic acids such as phthalic acid, isophthalic acid, terephthalic acid, malonic acid, succinic acid, malic acid, glutaric acid, adipic acid or sebacic acid in accordance with conventional esterification methods.

Di-(TCD-methylol)adipate has been shown to be especially suitable as a main constituent for immersion oils. Here, the percent by weight of the di-(TCD-methylol)adipate is at least 60%. As further components for adjusting the refractive index, butylbenzylphthalate and/or di-(propyleneglycol-1,2)dibenzoate can, for example, be added. The di-(TCD-methylol)adipate is likewise odorless as the other di-(TCD-methylol)ester in contrast to tricyclodecane alcohols and has no significant irritation with respect to human skin.

DESCRIPTION OF THE PREFERRED EMBODIMENTS OF THE INVENTION

There are many substances having the base structure of the tricyclodecanes whose ester derivatives or ether derivatives can be considered for the immersion oil of the invention. The structure formulas of such substances are shown in FIGS. 1a to 1c. The substances shown can be a TCD-monomer (FIGS. 1a and 1b) or a TCD-oligomer or a TCD-polymer (see FIG. 1c) for which the ring structure repeatedly occurs n-times. The ring structure is enclosed by brackets in FIG. 1c. One or several hydrogen atoms of the TCD-skeleton can, furthermore, and as shown in FIGS. 1a and 1b, be substituted by a residual R. Examples of suitable residuals R are presented in Table III. The substitution of the hydrogen by residual R has only a subordinate influence on the physical characteristics which are important for immersion oils.

The starting point for the ester synthesis can be TCD-alcohols (wherein X identifies an alcohol residual, preferably OH or CH₂ OH) or TCD carboxylic acids (wherein X identifies a carboxylic acid residual, preferably (COOH)₂. Examples of TCD-alcohols known in the literature are presented in Table IV. Here, TCD-monoalcohols, TCD-dialcohols as well as TCD-trialcohols can be used. The TCD-alcohol DM (dialcohol) and the TCD-alcohol M (monoalcohol) are, however, preferred because of their large-scale availability. The corresponding TCD-esters can be produced by converting the TCD-alcohols with a carboxylic acid in accordance with conventional synthesis methods. Suitable monocarboxylic acids, dicarboxylic acids or tricarboxylic acids are presented in Table V. The subsequent purification of the TCD-esters takes place with vacuum or high vacuum distillation. The temperature stability and the high boiling point of the di-(tricyclodecanemethylol)ester (boiling point over 200° C. at a pressure of 10⁻⁵ mbar) is of special significance. From this, excellent vacuum distillation results.

One can proceed from TCD-carboxylic acids as an alternative to ester synthesis from TCD-alcohols. Suitable TCD-monocarboxylic acids and TCD-dicarboxylic acids known from the literature are presented in Table VI. In this case, the esterification takes place by conversion with a monofunctional or a higher alcohol. Suitable alcohols are presented in Table VII.

In the same manner as with the synthesis of the TCD-esters, the corresponding ethers can be produced via conversion of the TCD-monoalcohols in accordance with conventional ether synthesis methods. The TCD-monoalcohols are presented in Table IV.

BRIEF DESCRIPTION OF THE DRAWINGS

In FIG. 2, the structure of di-(TCD-methylol)esters in general are shown and, in FIG. 3, the structures of di-(TCD-methylol)adipate are shown. The TCD-groups can themselves have the structures shown in FIGS. 1a to 1c with the residuals R presented in Table III.

The physical characteristics of several preferred di-(TCD-methylol)esters are presented in Table Ia with the characteristics being important for the immersion oils. The refractive index n_(e) >1.5 and the simultaneously high Abbe number v_(e) >=46 (v_(e) =47 for the di-(TCD-methylol)malinate) and even Abbe numbers v_(e) >50 for the other given di-(TCD-methylol)esters are essential for the superb suitability of aliphatic di-(TCD-methylol)esters as the main constituent of immersion oils. Furthermore, the excellent UV-transmissibility of the di-(TCD-methylol)esters is significant. This excellent UV-transmissibility is only for wavelengths under 320 nm for a 10 mm layer thickness at less than 10% transmission.

Table Ib shows a comparison of the physical characteristics of an immersion oil of the invention and known halogen-containing and halogen-free immersion oils. The composition of the immersion oil of the invention is presented under number 11 in Table II.

In Table II, the compositions and the physical characteristics of 14 preferred mixtures of a di-(TCD-methylol)ester and one or several high-boiling liquids is presented. The percent by weight of the di-(TCD-methylol)ester for the two component mixtures is between 68 and 98.5 percent by weight and, for the 3-component mixtures, between 51 and 70 percent by weight. As shown by the numerical values for the Abbe number and for the viscosity, almost any desirable viscosity value between 100 mm² /s and 6000 mm² /s for Abbe numbers in the range of 39 to 50 can be adjusted. Mixtures having viscosities in the range of 400 mm² /s to 600 mm² /s and therefore the embodiments 6, 11 and 12 are especially preferred for most applications.

In principle, the immersion oil can be put together from several di-(TCD-methylol)esters as a main constituent and several high-boiling liquids as a minor constituent to adjust the refractive index. The starting substances for a low residual fluorescence must be prepared in high purity and the usable quantities are relatively low. For this reason, the two-substance mixture is especially preferred when lower production costs are wanted.

German patent application P 196 08 081.9, filed Mar. 2, 1996, on which the claim of priority herein is based, is incorporated herein by reference.

It is understood that the foregoing description is that of the preferred embodiments of the invention and that various changes and modifications may be made thereto without departing from the spirit and scope of the invention as defined in the appended claims.

                                      TABLE Ia                                     __________________________________________________________________________     Physical Characteristics of Di (TCDmethylol)-esters                            __________________________________________________________________________                                Dispersion                                                                           Viscosity                                                  Refractive Indices                                                                           (Abbe -                                                                              at                                                         at 20° C.                                                                             No.) ζe                                                                         20° C.                                 Substance    n.sub.D (589,3 nm)                                                                    n.sub.D (546,1 nm)                                                                    DIN 58 884                                                                           DIN 51 562                                    __________________________________________________________________________     Di-(TCDmethylol)phthalate                                                                   1.5497 1.5533 39    ca. 280000 mPa*s                              Di-(TCDmethylol)malonate                                                                    1.5166 1.5191 51    1900 mm.sup.2 /s                              Di-(TCDmethylol)suoccinate                                                                  1.5149 1.5173 51    1600 mm.sup.2 /s                              Di-(TCDmethylol)glutarate                                                                   1.5137 1.5161 51    1300 mm.sup.2 /s                              Di-(TCDmethylol)adipate                                                                     1.5118 1.5142 51    1100 mm.sup.2 /s                              Di-(TCDmethylol)sebaoate                                                                    1.5057 1.5082 51     800 mm.sup.2 /s                              Di-(TCDmethylol)maleinate                                                                   1.5258 1.5284 47    9000 mm.sup.2 /s                              For Comparison:                                                                             1.5169 105192 52    1100 mPa*s                                    TCD-Alcohol M                                                                  __________________________________________________________________________                  Limit of UV - Permeability                                                     at d = 10 mm  Other                                               Substance    T ≦ 10%                                                                               Characteristics                                     __________________________________________________________________________     Di-(TCDmethylol)phthalate                                                                   at 319 nm                                                         Di-(TCDmethylol)malonate                                                                    at 276 nm     Boiling Point:180-185° C.                                 and Absorption Bands at 302 nm                                                               at 10.sup.-5 mbar                                   Di-(TCDmethylol)suoccinate                                                                  at 287 nm                                                         Di-(TCDmethylol)glutarate                                                                   at 286 nm                                                         Di-(TCDmethylol)adipate                                                                     at 262 nm     Boiling Point:220-225° C.                                               at 10.sup.-5 mbar                                                              Pourpoint: -20° C. (ISO 3016)                                           Flash Point (COC): 265° C.                                              (ISO 2592)                                                                     Density D.sub.20 = 1.090 g/cm.sup.3                                            (DIN 51 757)                                        Di-(TCDmethylol)sebaoate                                                                    at 260 nm                                                         Di-(TCDmethylol)maleinate                                                                   at 317 nm                                                                                    Boiling Point: 226° C.                                                  at 1013 mbar                                        For Comparison:                                                                             at 238 nm     Pourpoint: -24° C.                                                      Flash Point (COC): 130° C.                   TCD-Alcohol M                                                                               Density D20 = 1.044g/cm.sup.3                                     __________________________________________________________________________

                                      TABLE Ib                                     __________________________________________________________________________     Physical Data of Immersion Oils                                                                                       Immersion Oil                                                                  of the Invention                                 CARL ZEISS                                                                             Cargille                                                                              Cargille                                                                              Cargille                                                                               according to                                     Immersion Oil                                                                          Immersion Oil                                                                         lmmersion Oil                                                                         Immersion Oil                                                                          Tab. II,                                         518 C   Type A Type B Type DF Nr. 11                                  __________________________________________________________________________     Chemical Basis                                                                          Chlorinated                                                                            aliphatic                                                                             aliphatic                                                                             Chlorinated                                                                            Di-(TCDmethylol)-                                paraffins,                                                                             Hydrocarbons,                                                                         Hydrocarbons,                                                                         Paraffins, alkyl-                                                                      adipate                                          Phthalic acid ester                                                                    Terphenyls,                                                                           Terphenyls,                                                                           phthalate,                                                                             Butylbenzyl-phthalate                                    hydrated                                                                              hydrated                                                                              Butylbenzyl-                                                     Terphenyls                                                                            Terphenyls                                                                            phthalate                                       containing                                                                              yes     no     no     yes     no                                      halogens                                                                       n.sup.23.sub.D                                                                          1.5151  1.5150 1.5150 1.5152  1.5152                                  n.sup.23.sub.e                                                                          1.5180  1.5181 1.5180 1.5183  1.5180                                  Dispersion ζe                                                                      43.5    41     42.5   41.5    45.5                                    Kinematic                                                                               460     180    1700   440     560                                     Viscosity at                                                                   20° C. (mm.sup.2 /s)                                                    UV-Permeability                                                                at d = 10 mm (%)                                                               Transmission                                                                   (against water)                                                                • at 420 nm                                                                       94      86     88     96.5    >99                                     • at 400 nm                                                                       89      65     78     94      99                                      • at 380 nm                                                                       78      46     60     89      98                                      • at 365 nm                                                                       64      18     37     81      97                                      • at 350 nm                                                                       41      <5     <5     70      93                                      • at 330 nm                                                                       <8      <0.1   <0.1   45      85                                      Residual                                                                       fluorescence                                                                   (mg/l quinine sulfate                                                          equivalent amount)                                                             • F 365/450 nm                                                                    0.15-0.25                                                                              0.42   0.40   0.21    0.020                                   • F 405/485 nm                                                                    4.5-6.5 140    140    5.8     0.65                                    __________________________________________________________________________

                                      TABLE II                                     __________________________________________________________________________     Embodiments for halogen-free Immersion Oils                                                      Weight                                                                             Refractive indices                                                                          Dispersion                                                                           Viscosity                                               portions                                                                           at 23° C.                                                                            (Abbe-No.)                                                                           at 20° C.                      Example                                                                             Components   (Wt-%)                                                                             n.sub.D (589.3 nm)                                                                    n.sub.e (546.1 nm)                                                                   ζe                                                                              (mm.sup.2 /s)                         __________________________________________________________________________     1    Di-(TCDmethylol)phthalate                                                                   7.0                                                               Polypropyleneglycol (1,2) 400                                                               30  1.5150 1 .5181                                                                              40    6000                                  2    Di-(TCDmethylol)phthalate                                                                   58                                                                Dioctylphthalate                                                                            42  1.5150 1.5182                                                                               39    960                                   3    Di-(TCDmethylol)malonate                                                                    98.5                                                              Paraffin oil 1.5 1.5150 1.5176                                                                               50    1400                                  4    Di-(TCDmethylol)malonate                                                                    97.5                                                              Dioctylphthalate                                                                            2.5 1.5150 1.5176                                                                               50    1350                                  5    Di-(TCDmethylol)succinate                                                                   88.5                                                              Butylbenzylphthalate                                                                        11.5                                                                               1.5150 1.5177                                                                               48    810                                   6    Di-(TCDmethylol)succinate                                                                   70                                                                Butylbenzylphthalate                                                                        24.5                                                                               1.5150 1.5179                                                                               44    440                                        Dioctylsebacate                                                                             5.5                                                          7    Di-(TCDmethylol)succinate                                                                   66.5                                                              Dibenzylether                                                                               22.0                                                                               1.5150 1.5180                                                                               42    100                                        Dioctylsebacate                                                                             11.5                                                         8    Di-(TCDmethylol)maleinate                                                                   84                                                                Paraffin oil 16  1.5150 1.5178                                                                               48    2500                                  9    Di-(TCDmethylol)maleinate                                                                   89.5                                                              Dioctylsebacate                                                                             10.5                                                                               1.150  1.5178                                                                               47    1800                                  10   Di-(TCDmethylol)glutarate                                                                   90                                                                Butylbenzylphthalate                                                                        10  1.5150 1.5177                                                                               49    820                                   11   Di-(TCDmethyloI)adipate                                                                     83                                                                Butylbenzylphthalate                                                                        17  1.5150 1.5178                                                                               45    560                                   12   Di-(TCDmethylol)adipate                                                                     71.5                                                              Di-(propyleneglycol-                                                                        28.5                                                                               1.5150 1.5179                                                                               43    510                                        1,2)dibenzoate                                                            13   Di-(TCDmethylol)sebacate                                                                    68                                                                Butylbenzylphthalate                                                                        32  1.5150 1.5180                                                                               42    300                                   __________________________________________________________________________

                  TABLE III                                                        ______________________________________                                         Organic Groups (FIGS. 1a and 1b)                                               ______________________________________                                         X = CH.sub.2 OH,COOH                                                           R = H,CH.sub.3,C.sub.2 H.sub.5,C.sub.3 H.sub.7,C.sub.4 H.sub.9,C.sub.5         H.sub.11                                                                       C.sub.6 H.sub.13,C.sub.7 H.sub.15,C.sub.8 H.sub.17,C.sub.9 H.sub.19,C.sub.     10 H.sub.21                                                                    CH.sub.2CHCH.sub.2,CHCH.sub.2,CHCHCH.sub.3                                     CH.sub.2CHCHCH.sub.3,OH                                                        OCH.sub.3,OC.sub.2 H.sub.5,OC.sub.3 H.sub.7,OC.sub.4 H.sub.9,                  OC.sub.5 H.sub.11,OC.sub.6 H.sub.13                                             ##STR1##                                                                       ##STR2##                                                                       ##STR3##                                                                       ##STR4##                                                                       ##STR5##                                                                       ##STR6##                                                                       ##STR7##                                                                       ##STR8##                                                                       ##STR9##                                                                       ##STR10##                                                                      ##STR11##                                                                      ##STR12##                                                                      ##STR13##                                                                      ##STR14##                                                                      ##STR15##                                                                      ##STR16##                                                                      ##STR17##                                                                      ##STR18##                                                                      ##STR19##                                                                      ##STR20##                                                                      ##STR21##                                                                      ##STR22##                                                                      ##STR23##                                                                      ##STR24##                                                                      ##STR25##                                                                      ##STR26##                                                                      ##STR27##                                                                      ##STR28##                                                                      ##STR29##                                                                     ______________________________________                                    

                                      TABLE IV                                     __________________________________________________________________________     TCD - Alcohols                                                                 __________________________________________________________________________     TCD-(Mono)alcohols:                                                             ##STR30##                                                                      ##STR31##                                                                      ##STR32##                                                                      ##STR33##                                                                      ##STR34##                                                                     TCD-Di-Alcohols:                                                                ##STR35##                                                                      ##STR36##                                                                      ##STR37##                                                                      ##STR38##                                                                      ##STR39##                                                                      ##STR40##                                                                     TCD - tri-Alcohols                                                              ##STR41##                                                                      ##STR42##                                                                     __________________________________________________________________________

                                      TABLE V                                      __________________________________________________________________________     TCD - Carboxylic acids                                                         __________________________________________________________________________     TCD-(Mono)Carboxylic acids:                                                     ##STR43##                                                                      ##STR44##                                                                      ##STR45##                                                                     TCD-Dicarboxylic Acids:                                                         ##STR46##                                                                      ##STR47##                                                                      ##STR48##                                                                     __________________________________________________________________________

Literature Sources

B.Cornils, R. Payer: Derivate des Dicyclopentadiens--aktuelle Schlusselverbindungen Chemiker--Zeitung 98 70-76 (1974)

O. Roelen, K. Buchner et. al., Ruhrchemie Ag, Oberhausen: DBP 934 889 (1955) Verfahren zur Herstellung von Estern und bzw. oder Polyestern der Tricyclodekanreihe.

O. Roelen, K. Buchner et. al., Ruhrchemie AG, Oberhausen: DAS 1036 849 (1956) Verfahren zur Herstellung von als Schmiermittel, Weichmacher oder Polyester geeigneten Estern des Di-(tricyclo- 5.2.1.0²,6 !decyl)-8,8'ather4,4'-dimethylols, bzw. der Di-(tricyclo- 5.2.1.0²,6 !decyl-)-8,8'-ather4,4'-dicarbonsaure.

J. Bartlett, R. Brodkey et. al.: U.S. Pat. No. 2,814,639 (1957) Dimethylol--Tricyclodecanol Esters and Process.

British Petroleum Co. Ltd. Brit. Pat. 847 592 (1960) New Polyesters and their method of preparation.

                                      TABLE VI                                     __________________________________________________________________________     Carboxylic Acid for the Synthesis of TCD - Esters                              Monocarboxylic Acids:                                                          formic acid          2,2-dimethyl-4-pentene acid                               acetic acid          2-hexene acid                                             propionic acid       3-hexene acid                                             n/isobutyric acid    2-heptene acid                                            n/iso-valeric acid   6-heptene acid                                            hexanoic acid        2-octene acid                                             heptanoic acid       4-ethyl-2-octene acid                                     octanoic acid        2-nonene acid                                             nonanoic acid        2-decene acid                                             decanoic acid        ethoxy acetic acid                                        undecanoic acid      3-ethoxy-propionic acid                                   dodecanoic acid      L-menthoxy-acetic acid                                    pivalic acid         cyclopropanecarboxylic acid                                                    2-methylcyclopropane carboxylic acid                      2-methylbutyric acid cyclobutane carboxylic acid                               3-methylbutyric acid cyclopentane carboxylic acid                              2,2-dimethylbutyric acid                                                                            cyclohexane carboxylic acid                               3,3-dimethylbutyric acid                                                                            cycloheptane carboxylic acid                              tertiary butyl acetic acid                                                                          cyclooctane carboxylic acid                               2-ethyl butyric acid cycloundecanoic carboxylic acid                           2-methyl valeric acid                                                                               cyclopentyl acetic acid                                   3-methyl valeric acid                                                                               cyctohexyl acetic acid                                    4-methyl valeric acid                                                                               3-cyclopentyl propionic acid                              2,2-dimethyl valeric acid                                                                           tetrahydrofurane-2-carboxylic acid                        2-propyl valeric acid                                                                               tetrahydrofurane-3-carboxylic acid                        2-methyl hexanoic acid                                                                              2-tetrahydroxyfurane acetic acid                          2-ethyl hexanoic acid                                                                               1 (2,3,4) methyl-1-cyclohexane carboxylic acid            Di-(n-propyl-)acetic acid                                                                           4-cyclohexyl butyric acid                                 crotonic acid        2-cyclohexyl butyric acid                                 vinylacetic acid     (α- ethyl!cyclohexane acetic acid)                  2-methyl crotonic acid                                                                              2-norborane acetic acid                                   3,3-dimethyl acrylic acid                                                                           tricyclo 5.2.1.0.sup.2,6 !decane-2carboxylic acid         (3-methyl crotonic acid)                                                                            tricyclo 5.2.1.0.sup.2,6 !decane-3(4)carboxylic                                acid                                                      2-pentene acid       (TCD-acid S)                                              4-pentene acid       Tricyclo 5.2.1.0.sup.2,6 !decane8(9)carboxylic acid       2-methyl-2-pentene acid                                                                             Adamantane carboxylic acid                                1-adamantane acetic acid                                                                            2-phenylcyclopropane-1-carboxylic acid                    3-cyclohexene-1-carboxylic acid                                                                     1 -phenylcyclobutane carboxylic acid                      4-cycloheptene-1 -carboxylic acid                                                                   1-phenyl-1 -cyclohexane carboxylic acid                   4-cyclooctene-1-carboxylic acid                                                                     cyclohexylphenyl acetic acid                              1 -cycloundecene-1-carboxylic acid                                                                  diphenyl acetic acid                                      exo-bicyclo 2.2.1!hept-5-ene-2carboxylic acid                                                       3,3-diphenylpropionic acid                                (exo-5-Norbornene-2-carboxylic acid)                                                                2,2-diphenylpropionic acid                                5-norbornene-2-acrylic acid                                                                         4-phenylvaleric acid                                      3-camphor carboxylic acid                                                                           5-phenylvaleric acid                                      2-cyclopentene-1yl-acetic acid                                                                      phenoxy acetic acid                                       2,2,3,3-tetramethylcyclopropane carboxylic acid                                                     3-phenoxypropionic acid                                   4-acetylbutyric acid 2-phenoxybutyric acid                                     3-methyl-2-oxovaleric acid                                                                          4-phenoxybutyric acid                                     4-methyl-2-oxovaleric acid                                                                          11-phenoxyundecanoic acid                                 5-acetylvaleric acid 3-benzoylpropionic acid                                   2-oxopentanoic acid  4-benzoylbutyric acid                                     2-oxohexanoic acid   5-benzoylvaleric acid                                     7-oxooctanoic acid   2-phenyllevulinic acid                                    5-oxodecanoic acid   o-toluic acetic acid                                      7-oxodecanoic acid   m-toluic acetic acid                                      2-ethylhexoxy acetic acid                                                                           p-toluic acetic acid                                      3,6-dioxa heptanoic acid                                                                            di-p-toluic acetic acid                                   3,6,9-trioxa decanoic acid                                                                          1-indane carboxylic acid                                  3-methoxycyclohexanoic carboxylic acid                                                              1,2,3,4-tetrahydro-1(2)-naphthalene carboxylic                                 acid                                                      4-methoxycyclohexanoic carboxylic acid                                                              2-methoxyphenyl acetic acid                               phenyl acetic acid   3-methoxyphenyl acetic acid                               2-phenyl propionic acid                                                                             4-methoxyphenyl acetic acid                               3-phenylpropionic acid                                                                              p-ethoxyphenyl acetic acid                                benzoic acid         3-(o-methoxyphenyl)propionic acid                         2(3,4)-methylbenzoic acid                                                                           3-(p-methoxyphenyl)propionic acid                         (toluic acid)        4-(p-methoxyphenyl)butyric acid                           2(3,4)biphenylcarboxylic acid                                                                       1 -m-toluiccyclopentanoic carboxylic acid                 1(2)-naphthalene carboxylic acid                                                                    1-(p-toluic)-1-cyclopropane carboxylic acid               2-phenylbutyric acid 1-(p-toluic)-1-cyclobutane carboxylic acid                3-phenylbutyric acid 1-(p-toluic)-1-cyclopentane carboxylic acid               4-phenylbutyric acid 1-(p-toluic)-1-cyclohexane carboxylic acid                1-phenylcyclopentane carboxylic acid                                                                1-(p-methoxyphenyl)-1-cyclopropane carboxylic                                  acid                                                      α-cyclopentyl-phenyIacetic acid                                                               1-(p-methoxyphenyl)-1-cyciopentane carboxylic                                  acid                                                      1-phenyl-1 -cyclopropane carboxylic acid                                                            1-(p-methoxyphenyl)-1-cyclohexane carboxylic                                   acid                                                      4-ethoxy--3-methoxyphenyl acetic acid                                                               octanedioic acid                                          (3,4-dimethQxyphenyl)acetic acid                                                                    (suberic acid)                                            (2,5-dimethoxyphenyl)acetic acid                                                                    nonanedioic acid                                          3(3,4-dimethoxyphenyl)propionic acid                                                                (azelaic acid)                                            3,4,5-trimethoxyphenyl acetic acid                                                                  decanedioic acid                                          1-naphthyl acetic acid                                                                              (sebacic acid)                                            2-naphthyl acetic acid                                                                              undecanedioic acid                                        (2-naphthoxy)acetic acid                                                                            dodecanedioic acid                                        2,3-/2,6/3,4/2,4/2,5-dimethylbenzoic acid                                                           tridecanedioic acid                                       2(3,4)-methoxybenzoic acid                                                                          (brassylic acid)                                          2,342,6/3,4/2,4/2,5-dimethoxybenzoic acid                                                           tetradecanedioic acid                                     2(2,4)-ethoxybenzoic acid                                                                           methylmalonic acid                                        p-tert.-butyl-benzoic acid                                                                          dimethylmalonic acid                                      p-n-butoxybenzoic acid                                                                              ethylmalonic acid                                         p-cyciohexyloxybenzoic acid                                                                         propylmalonic acid                                        4-acetylbenzoic acid diethylmalonic acid                                       3-methoxy-4-methyl-benzoic acid                                                                     butylmalonic acid                                         3,4(methylenedioxy)benzoic acid                                                                     (2-cyclopentene-1-yl)malonic acid                         (piperonylic acid)   phenylmalonic acid                                        3,4,5-trimethoxybenzoic acid                                                                        benzylmalonic acid                                        2,4,6-trimethoxybenzoic acid                                                                        methylsuccinic acid                                       2,4,5-trimethoxybenzoic acid                                                                        methylene succinic acid                                   2-benzylbenzoic acid (itaconic acid)                                           o-phenoxybenzoic acid                                                                               1-octadecenylsuccinic acid                                2-bibenzylcarboxylic acid                                                                           2,2dimethylsuccinic acid                                  (o-phenethylbenzoic acid)                                                                           2,3dimethylsuccinic acid                                  1-methylindene-2-carboxylic acid                                                                    2-methylglutaric acid                                     9-fluorene carboxylic acid                                                                          3-methylglutaric acid                                     xanthene-10-carboxylic acid                                                                         2,2-dimethylglutaric acid                                 dicarboxylic acids:                                                            malonic acid         3,3-dimethylglutarlc acid                                 succinic acid        2,4-dimethylglutaric acid                                 maleic acid          2,3-dimethylglutanic acid                                 (toxii acid)         2,3-dimethylmaleic acid (cis)                             fumaric acid         2,3-dimethylfumaric acid (trans)                          glutaric acid        methylmaleic acid                                         glutacon acid        (citraconic acid)                                         adipic acid          methylfumaric acid                                        3-hexenediacid (hydromuconic acid)                                                                  (mesaconic acid)                                          heptanedioic acid (pimelic acid)                                                                    phenylmaleic acid                                         2-ethyl-2-methylsuccinic acid                                                                       cyclohexane-1,4-dicarboxylic acid                         phenylsuccinic acid  4-methylhexahydrophthalic acid                            3-methyladipic acid  1,1-cyclohexanediacetic acid                              2,5-dimethyladipic acid                                                                             cis/trans-4-cyclohexene-1,2-dicarboxylic acid             hydroxysuccinic acid exo/endo-5-norbornene-2,3-dicarboxylic acid               (DL-malic acid)      methyl-5-norbornene-2,3-dicarboxylic acid                 2-hydroxy-2-isopropylsuccinic acid                                                                  exo-7-oxabicyclo 2.2.1!hept-5-ene-2,3-dicarboxylic                             acid                                                      sulphosuccinic acid  =exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic acid            3-hydroxy-3-methylglutaric acid                                                                     1,3-adamantanediacetic acid                               2,2,5,5-tetramethyladipic acid                                                                      phthalic acid                                             2-oxoglutaric acid   isophthalic acid                                          (ketoglutaric acid)  terephthalic acid                                         2-oxoadipic acid     4-methylphthalic acid                                     (α-ketoadipic acid)                                                                           2-methoxyisophthalic acid                                 3-oxoadipic acid     5-methylisophthalic acid                                  (β-ketoadipic acid)                                                                            5-tert.butylisophthalic acid                              4-oxoheptanedioic acid                                                                              3-phenylglutaric acid                                     (4-ketopimelic acid) TCD-carboxylic acid DS =                                  acetonedicarboxylic acid                                                                            tricycio 5.2.1.0.sup.2,6 !decane-3(4),8(9)-dicarboxyl                          ic acid                                                   (3-oxoglutaric acid) 8,8'-di(tricyclo 5.5.1.0.sup.2,6 !decyl)ether-            3,6-dioxaoctanedioic acid                                                                           3(4),3'(4')-dicarboxylic acid                             (3,6-dioxasuberic acid)                                                                             tetramethylterephthalic acid                              3,6,9-trioxaundecanedioic acid                                                                      o,m,p-phenylenedioic acetic acid                          diglycolic acid      o,m,p-phenylenedioxydioic acetic acid                     (oxadiethanoic acid) o,m,p-carboxyphenoxyacetic acid                           DL-tartaric acid     p-phenylenedipropionic acid                                                    2,5-dihydroxybenzol-1,4-diacetic acid                     2,2'-thiodiacetic acid                                                                              diphenyldisulfid-2,2'-dicarboxylic acid                   (thiodiglycolic acid)                                                                               (2,2'-dithiosalicylic acid)                               3,3'-thiodipropionic acid                                                                           diphenylcarboxylic acid                                   3,3'-dithiodipropionic acid                                                                         1,5-decalindicarboxylic acid                              cyclopropane-1,1-dicarboxylic acid                                                                  (5-dihydroxydecahydronaphthalene)                         cyclobutane-1,1-dicarboxylic acid                                                                   1,8-naphthalic acid                                       cyclobutane-1,2-dicarboxylic acid                                                                   (naphthalene-1,8-dicarboxylic acid)                       3,3 tetramethyleneglutaric acid                                                                     2,3-naphthaiene-dicarboxylic acid                         cyclopentane-1,2-dicarboxylic acid                                                                  1,4-naphthalene-dicarboxylic acid                         camphoric acid       2,6-naphthalene-dicarboxylic acid                         cyclohexane-1,2-dicarboxylic acid                                                                   1,5-naphthalene-dicarboxylic acid                         cyclohexane-1,3-dicarboxylic acid                                              Tricarboxylic Acids:                                                           1,2,3-propane tricarboxylic acid                                                                    citric acid                                               (tricarballylic acid)                                                                               1,2,4-benzoltricarboxylic acid                            2-methyl-1,2,3-propanetricarboxylic acid                                                            (trimellitic acid)                                        (α-methyl-tricarboxylic acid)                                                                 1,3,5-benzoltricarboxylic acid                            1,3,5-pentane tricarboxylic acid                                                                    (trimesitic acid)                                         1,2,3-propenetricarboxylic acid                                                (aconitic acid)                                                                __________________________________________________________________________

                                      TABLE VII                                    __________________________________________________________________________     Alcohols for the Synthesis of TCD - Esters and/or Ethers                       Mono - Alcohols:                                                               methanol            3-octanol           3-methyl-4-octanol                     ethanol             4-octanol           4-methyl-3-nonanol                     n/iso-propanol      2-nonanol           2-methyl-3-nonanol                     n/iso-butanol       3-nonanol           2-methyl-4-nonanol                     sec-butyl alcohol   4-nonanol           3-methyl-4-nonanol                     tert-butyl alcohol  5-nonanol           2-methyl-2-pentanol                    1-pentanol          2-decanol           3-methyl-3-pentanol                    1-hexanol           3-decanol           3-ethyl-3-pentanol                     1-heptanol          4-decanol           2,4-dimethyl-2-pentanol                1-octanol           5-decanol           2,3-dimethyl-3-pentanol                1-nonanol           2-methyl-2-butanol                                         1-decanol           (tert. amylic alcohol)                                                                             2,2,4-tnmethyl-3-pentanol              2-methyl-2-hexanol                                                             1-undecanol         3-methyl-2-butanol  3-methyl-3-hexanol                     1-dodecanol         3,3-dimethyl-2-butanol                                                                             2,3-dimethyl-3-hexanol                 2-methyl-1 -butanol 2,3-dimethyl-2-butanol                                                                             2,5-dimethyl-2-hexanol                 2,2-dimethyl-1-propanol                                                                            3-methyl-2-pentanol 3,4-dimethyl-3-hexanol                 (neopentylalcohol)  4-methyl-2-pentanol 3,5-dimethyl-3-hexanol                 2-methyl-1 -propanol                                                                               3-ethyl-2-pentanol  2-methyl-2-heptanol                    3-methyl-1-butanol  2-methyl-3-pentanol 3-methyl-3-heptanol                    2,2-dimethyl-1-butanol                                                                             2,2-dimethyl-3-pentanol                                                                            3-ethyl-3-heptanol                     3,3-dimethyl-1-butanol                                                                             2,4-dimethyl-3-pentanol                                                                            4-methyl-4-heptanol                    2-ethyl-1-butanol   3-methyl-2-hexanol  4-methyl-4-octanol                     3-methyl-1-pentanol 2-methyl-3-hexanol  4-methyl-4-nonanol                     4-methyl-1 -pentanoi                                                                               5-methyl-3-hexanol  3,5,5-trimethylhexanol                 2,2-dimethyl-1-pentanol                                                                            4-ethyl-3-hexanol   (isononylic aicohol                    2,3-dimethyl-1-pentanol                                                                            3,4-dimethyl-2-hexanol                                                                             crotylic alcohol                       2-ethylhexanol      2,2-dimethyl-3-hexanol                                                                             3-methyl-2-butene-1-ol                 2-ethyl-2-propylhexanol                                                                            2,5-dimethyl-3-hexanol                                                                             3-butene-1-ol                          2-pentanol          6-methyl-2-heptanol 2-methyl-3-butene-2-ol                 3-pentanol          S-ethyl-2-heptanol  4-pentene-1-ol                         2-hexanol           4-methyf-3-heptanol 4-pentene-2-ol                         3-hexanol           S-methyl-3-heptanol 1-pentene-3-ol                         2-heptanol          3-methyl-4-heptanol 3-pentene-2-ol                         3-heptanol          2,2-dimethyl-3-heptanol                                                                            4-methyl-3-pentene-2-ol                4-heptanol          2,4-dimethyl-3-heptanoI                                                                            4-methyl-1-pentene-3-ol                2-octanol           2-methyl-3-octanol  2-methyl-4-pentene-2-ol                2,3-dimethyl-4-pentene-2-ol                                                                           cyclo octanemethanol                                    2-hexene-1-ol          cyclo undecanemethanol                                  4,4-dimethyl-2-methylene-1-pentanol                                                                   cyclo dodecanemethanol                                  2-ethyl-2-hexene-1-ol  2-norbornanemethanol                                    4-hexene-3-ol          3-methylnorbornane-2-methanol                           1 -hexene-3-ol         1-adamantanemethanol                                    5-hexene-3-ol          6,6-dimethylbicyclo 3.1.1!hept-2-ene-2-ethanol                                 (napol)                                                 3-ethyl-5-hexene-3-ol                                                          3,5-dimethyl-5-hexene-3-ol                                                                            1-methyl cyclopentanol                                  3-heptene-1-ol         1-ethyl cyclopentanol                                   1-heptene-3-ol         1-(n-propyl)-1-cyclopentanol                            2-heptene-4-ol         1-(n-butyl)-1-cyclopentanol                             2-methyl-1-heptene-3-ol                                                                               2-cyclohexene-1-ol                                      4-methyl-1-heptene-4-ol                                                                               1 -methylcyclohexanol                                   1-octene-3-ol          2-methylcyclohexanol                                    1-octene-4-ol          2-ethylcycIohexanol                                     3,7-dimethyl-6-octene-l-ol                                                                            3-methylcyclohexanol                                    (citronellol)          4-methylcyclohexanol                                    cyclo butane-1-ol      4-ethylcyclohexanol                                     cyclopropylmethylcarbinol                                                                             4-tert. butylcyclohexanol                               dicyclopropylcarbinol  2,3-dimethylcyclohexanol                                cyclobutanol           2,5-dimethylcyclohexanol                                cyclopentanol          2,4-dimethylcyclohexanol                                cyclohexanol           2,6-dimethylcyclohexanol                                cycloheptanol          3,5-dimethylcycIohexanol                                cyclooctanol           3,4-dimethylcycIohexanol                                cyclopentylmethanol    3,3,,5-trimethylcyclohexanol                            2-cyclopentylethanol   dl-menthol                                              1 cyclopentylethanol   p-menth-1-ene-9-ol                                      3-cyclopentyl-1-propanol                                                                              isopulegol                                              cyclohexylmethanol     bornyl alcohol, isoborneol                              2-methylcyclopentanol  myrtanol                                                1-cyclohexylethanol    1-methylcyclooctanol                                    1-cyclohexyl-1-propanol                                                                               cyclododecanol                                          1-cyclohexyl-1-butanol norborneol                                                                     (endo/exo)                                              2-cyclohexylethanol                                                            3-cyclohexene-1-methanol                                                                              5-norbornene-2-ol                                       3-cyclohexene-1-ethanol                                                                               borneol                                                 cycloheptanemethanol                                                           TCD-alcohol A          1-phenyl-1-pentanol                                     = 5-hydroxy-tricyclo  5.2.1.0.sup.2,6 !decane                                                         cyclopropylphenylcarbinol                               3(4)-hydroxy4ricyclo 5.2.1.026!decane                                                                 1 cyclopropyl--methylbenzylalcohol                      TCD-alcohol M          cyclohexylphenylcarbinol                                = 8-hydroxymethylcyclo 5.2.1.0.sup.2,6 !decane                                                        1-phenyl-1-cyclohexanol                                 3(4)-hydroxymethyl-tricyclo 5.2.1.0.sup.2,6 !decane                                                   2-phenyl-1-cyclohexanol                                 TCD alcohol E          benzhyd rol                                             = 8(9)-hydroxy-tricyclo 5.2.1.0.sup.2,6 !dec-3-ene                                                    1,1-dlphenylethanol                                     5-hydroxy-tricyclo 5.2.1.0.sup.2,6!dec-3-ene                                                          α-benzylbenzhydrol                                1-adamantanol          o-phenyethylbenzylalcohol                               2-adamantanol          2-methoxybenzylalcohol                                  decahydro-1 (2)-naphthol                                                                              3-methoxybenzylalcohol                                  di-2-norbornylmethanol 4-menthoxybenzylalcohol                                 2-methoxyethanol       4-methylbenzylalcohol                                   2-ethoxyethanol        p-tert. butylbenzylatcohol                              2-propoxyethanol       p-butoxybenzylalcohol                                   2-butoxyethanol        p-dimethylbenzytalcohol                                 3-ethoxy-1-propanol    p-methyl-α-(n-propyl)benzylalcohol                3-methoxy-1-butanol    4,4'-dimethoxybenzylalcohol                             2-isopropyloxyethanol  o-phenoxybenzylalcohol                                  1 ,3-diethoxy-2-propanol                                                                              p-methoxy-α-methylbenzylalcohot                   diethyleneglycolmonomethylether                                                                       p-methoxy-α-ethylbenzylalcohol                    (methyldiglycol)       α-cyclopropyt-p-methylbenzylalcohol               diethyleneglycolmonoethylether                                                                        (cyclopropyl-p-toluic carbinol)                         (ethyldiglycol)        α-cyclopropyl-α,p-dimethytbenzylalcohol     diethyteneglycolmonobutylether                                                                        α-cyctopropyl-p-methoxybenzylalcohol              (butyldiglycol)        2,3-dimethoxybenzylalcohol                              4-ethoxy-1-decalol     2,4-dimethoxybenzylalcohol                              3-hydroxytetrahydrofurane                                                                             3,4-dimethoxybenzylalcohol                              tetrahydroxyfurfurylalcohol                                                                           3,5-dimethoxybenzylalcohol                              tetrahydropyrane-2-methanol                                                                           3,4-methylenedioxyphenylmethanol                        2,2-dimethyl-1,3-dioxolane                                                                            (Piperonylic alcohol)                                   (solketal)             3,4,5-trimethoxybenzylalcohol                           diacetonealcohol       4-biphenylmethanol                                      benzylalcohol          (p-phenylbenzylalcohol)                                 α-methytbenzylalcohol                                                                           m(p)-benzyloxybenzylalcohot                             α,α-dimethylbenzylatcohol                                                                 1,2,3,4-tetrahydro-1-naphthot                           α-ethylbenzytalcohol                                                                            benzo-2,3-dihydroxypyrane-4-ot                          1-phenyl-1-butanol     (4-chromanol)                                           2-hydroxymethyl-1 ,4-benzodioxane                                                                     2-phenyl-1-propanol                                     1(2)-naphthalenemethanol                                                                              β-ethylphenethylalcohol                            9-fluorenemethanol     3-phenyl-1-propanol                                     1-fluorenemethanol     3,3-diphenyl-i-propanol                                 9-hydroxyfluorene      benzyl-tert. butanol                                    1-acenaphthenol        2-phenoxyethanol                                        dibenzosuberol         1-naphthalinethanol                                     9-anthracenemethanol   1(o-benzylphenoxy)-2-propanol                           phenethylalcohol                                                               Dialcohols (Dioles)                                                            ethylenegycol          1,12-dodecanediol                                       1,2-propanediol        cyclohexane-1,1-dimethanol                              1,3-propanediol        3-cyclohexene-1,1-dimethanol                            2,2-dimethyl-1,3-propanediol                                                                          1,5-cyclooctanediol                                     (neopentylglycol)      2,2,4,4-tetramethyl-1,3-cyclobutanediol                 2,2-diethyl-1,3-propanediol                                                                           1,2-cyclohexanediol                                     2-ethyl-2-methyl-1,3-propanediol                                                                      1,3-cyclohexanediol                                     2-methyl-2-propyl-1,3-propanediol                                                                     1,4-cyclohexanediol                                     2-n-butyl-2-ethyl-1,3-propanediol                                                                     1,2-cycloheptanediol                                    1,4-butenediol         1,2-cyclododecanediol                                   2-methyl-1,4-butanediol                                                                               1,4-decalenediol                                        1,3-butanediol         1,5-decalenediol                                        1,2-butanediol         TCD-alcohol DM                                          2,3-butanediol         = 3(4),B(9)-bis(hydroxymethyl)tricyclo 5.2.1.02!dec                            ane                                                     pinacol                3(4),8(9)-bis(hydroxymethyl)tricyclo 5.2.1.0.sup.2,                            6 !decane                                               (1,3-dimethyl-2,3-butanediol)                                                                         TCD-alcohol OM                                          1,5-pentanediol        8-hydroxy-4(5)hydroxymethyl4ncyclo 5.2.1.0.sup.2,6                             !decane                                                 2,4-pentanediol        3,4-dihydroxytricyclo 5.2.1.0.sup.2,6 !decane           2-methyl-2,4-pentanediol                                                                              di-TCD-alcohol M)ether                                  1,6-hexanediol         = di(tricyclo 5.2.1.0.sup.2,6 !decyl-8,8'-ether-3(4                            ))dimethylol                                            2,5-hexanediol         di-TCD-alcohol A)ether                                  2-ethyl-1,3-hexanediol = di (tricyclo 5.2.1.0.sup.2,6 !decyl-8,8'-ether-3(                            4),3'(4'))diol                                          2,5-dimethyl-2,5-hexanediol                                                                           5,9-cyclododecanedien-1,2-diol                          1,7-heptanediol        2-butene-1,4-diol                                       1,8-octanediol         3-hexene-2,5-diol                                       1,9-nonanediol         1,2-cyclobutanedimethanol                               1,10-decanediol        1,4-cyclohexanedimethanol                               5-norbornene-2,2-dimethanol                                                                           4(2-hydroxyethoxy)-1-decatol                            diethyleneglycol       2,4-dihydro-2H-pyrane-2,2-dimethanol                    triethyleneglycol      1,2-benzoldimethanol                                    tetraethyleneglycol    1,3-benzoldimethanol                                    polyethyleneglycol     1,4-benzoldimethanol                                    dipropyleneglycol      tetramethyl-p-xylol--,&-diol                            polypropyleneglycol    2,2-diphenyl-1,3-propanediol                            polyletrahydrofurane   1-phenyl-1,2-ethanediol                                 (poly- 1,4-butanediol) (styreneolycol)                                         Polvalcohols (Polvoles)                                                        glycerol               pentaerylhrite                                          trimethylolethane      dipentaerylhrite                                        trimethylolpropane     meso-erylhritol                                         2-hydroxymethyl-2propyl-1,3propanediol                                                                TCD-atcohol TO                                          1,2,6-trihydroxyhexane = 8(9),3(4)-tri-hydroxy-tricyclo 5.2.1.0.sup.2,6                               !decane                                                 2,5-dimethyl-1,2,6-hexanetriol                                                                        8-hydroxy-4,4-dihydroxymethyl-tricycto 5.2.1.0.sup.                            2,6 !decane                                             __________________________________________________________________________ 

What is claimed is:
 1. An immersion oil for microscopy, the immersion oil comprising:as a main constituent, the tricyclodecane derivative or derivatives of substances having the basic structure of the tricyclodecane; said tricyclodecane derivative or derivatives being esters or ethers of tricyclodecanes or said tricyclodecane derivatives being esters or ethers of substances having base structures of tricyclodecanes; and, said immersion oil further including minor constituents comprising one or more high-boiling liquids.
 2. The immersion oil of claim 1, wherein said substances are tricyclodecanepolymers or tricyclodecaneoligomers.
 3. The immersion oil of claim 1, wherein the main constituent is selected from the group consisting of tricyclodecane-methylolesters and tricyclodecanemethylolethers.
 4. The immersion oil of claim 1, wherein said immersion oil further comprises minor constituents comprising one or more high-boiling liquids.
 5. The immersion oil of claim 4, wherein the high-boiling liquids are selected from the group consisting of paraffin oil, softeners, polypropylglycol, butylbenzylphthalate, dioctylphthalate, dioctylsebacate and di-(propyleneglycol-1.2)dibenzoate.
 6. The immersion oil of claim 1, wherein the portion of the tricyclodecane derivative or the derivative of substances having the base structure of the tricyclodecane is greater than 50% by weight.
 7. The immersion oil of claim 1, wherein the portion of the tricyclodecane derivative or the derivative of substances having the base structure of the tricyclodecane is greater than 60% by weight.
 8. Di-(tricyclodecanemethylol)adipate produced by esterification of 8(9)-hydroxymethyltricyclo 5.2.1.0²,6 !decane and adipic acid followed by vacuum distillation of the esters obtained.
 9. An immersion oil for microscopy, the immersion oil comprising:as a main constituent, the tricyclodecane derivative or derivatives of substances having the basic structure of the tricyclodecane; and, said main constituent being selected from the group consisting of: di-(tricyclodecane methylol)adipate, di-(tricyclodecane methylol)phthalate, di-(tricyclodecane methylol)malonate, di-(tricyclodecanemethylol)succinate, di-(tricyclodecane methylol)maleinate, di-(tricyclodecanemethylol)glutarate and di-(tricyclodecanemethylol)sebacate.
 10. The immersion oil of claim 9, wherein said immersion oil further comprises minor constituents comprising one or more high-boiling liquids.
 11. The immersion oil of claim 10, wherein the high-boiling liquids are selected from the group consisting of paraffin oil, softeners, polypropylglycol, butylbenzylphthalate, dioctylphthalate, dioctylsebacate and di-(propyleneglycol-1.2)dibenzoate.
 12. The immersion oil of claim 9, wherein the portion of the tricyclodecane derivative or the derivative of substances having the base structure of the tricyclodecane is greater than 50% by weight.
 13. The immersion oil of claim 9, wherein the portion of the tricyclodecane derivative or the derivative of substances having the base structure of the tricyclodecane is greater than 60% by weight.
 14. Di-(tricyclodecanemethylol)adipate having the formula: ##STR49##
 15. An immersion oil for microscopy, the immersion oil comprising:as a main constituent, di-(tricyclodecanemethylol)ester or di-(tricyclodecanemethylol)ether or substances having the basic structure of di-(tricyclodecanemethylol)esters or di-(tricyclodecanemethylol)ethers.
 16. The immersion oil of claim 15, wherein the main constituent is selected from the group consisting of: di-(tricyclodecane methylol)adipate, di-(tricyclodecane methylol)phthalate, di-(tricyclodecane methylol)malonate, di-(tricyclodecanemethylol)succinate, di-(tricyclodecane methylol)maleinate, di-(tricyclodecanemethylol)glutarate and di-(tricyclodecanemethylol)sebacate.
 17. The immersion oil of claim 15, wherein said immersion oil further comprises minor constituents comprising one or more high-boiling liquids.
 18. The immersion oil of claim 17, wherein the high-boiling liquids are selected from the group consisting of paraffin oil, softeners, polypropylglycol, butylbenzylphthalate, dioctylphthalate, dioctylsebacate and di-(propyleneglycol-1.2)dibenzoate.
 19. The immersion oil of claim 15, wherein the portion of the di-(tricyclodecanemethylol) ester or ether or substances having the basic structure of di-(tricyclodecanemethylol) esters or ethers is greater than 50% by weight.
 20. The immersion oil of claim 15, wherein the portion of the di-(tricyclodecanemethylol) ester or ether or substances having the basic structure of di-(tricyclodecanemethylol) esters or ethers is greater than 60% by weight. 